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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:32:19 UTC
Update Date2022-07-12 23:01:06 UTC
HMDB IDHMDB0029737
Secondary Accession Numbers
  • HMDB29737
Metabolite Identification
Common NameIndole-3-carboxaldehyde
DescriptionIndole-3-carboxaldehyde (IAld or I3A), also known as 3-formylindole or 3-indolealdehyde, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of a pyrrole ring fused to benzene to form 2,3-benzopyrrole. In humans, I3A is a biologically active metabolite which acts as a receptor agonist at the aryl hydrocarbon receptor in intestinal immune cells. It stimulates the production of interleukin-22 which facilitates mucosal reactivity (PMID:27102537 ). I3A is a microbially derived tryptophan metabolite produced by Clostridium and Lactobacillus (PMID:30120222 , 27102537 ). I3A has also been found in the urine of patients with untreated phenylketonuria (PMID:5073866 ). I3A has been detected, but not quantified, in several different foods, such as beans, Brussels sprouts, cucumbers, cereals and cereal products, and white cabbages. This could make I3A a potential biomarker for the consumption of these foods.
Structure
Data?1586965572
Synonyms
ValueSource
1H-Indole-3-carboxaldehydeChEBI
3-FormylindoleChEBI
3-IndolealdehydeChEBI
3-IndolecarbaldehydeChEBI
3-IndolecarboxaldehydeChEBI
beta-IndolylaldehydeChEBI
I3choChEBI
Indole-3-aldehydeChEBI
Indole-3-carbaldehydeKegg
b-IndolylaldehydeGenerator
Β-indolylaldehydeGenerator
3-IndolemethanalMeSH
1H-Indole-3-carbaldehydeHMDB
1H-Indole-3-carboxaldehdeHMDB
indol-3-CarbaldehydHMDB
indol-3-CarbaldehydeHMDB
indol-3-CarboxaldehydeHMDB
INDOLE-3-carboxyaldehydeHMDB
Indole-3-carboxaldehydeChEBI
1H-Indol-3-yl carboxaldehydeHMDB
1H-Indole-3-aldehydeHMDB
1H-Indole-3-methanalHMDB
3-Formyl-1H-indoleHMDB
3-IndolylformaldehydeHMDB
I3AHMDB
Indole-3-carboxylaldehydeHMDB
Indole-3-formaldehydeHMDB
Chemical FormulaC9H7NO
Average Molecular Weight145.158
Monoisotopic Molecular Weight145.052763851
IUPAC Name1H-indole-3-carbaldehyde
Traditional Nameindole-3-carboxaldehyde
CAS Registry Number487-89-8
SMILES
O=CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
InChI KeyOLNJUISKUQQNIM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Aryl-aldehyde
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point197 - 199 °CNot Available
Boiling Point339.10 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2927 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.68Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.46 g/LALOGPS
logP1.92ALOGPS
logP1.78ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)13.54ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.86 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.73 m³·mol⁻¹ChemAxon
Polarizability15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.02131661259
DarkChem[M-H]-127.46731661259
DeepCCS[M+H]+130.5130932474
DeepCCS[M-H]-127.19430932474
DeepCCS[M-2H]-164.37130932474
DeepCCS[M+Na]+139.61730932474
AllCCS[M+H]+129.932859911
AllCCS[M+H-H2O]+125.132859911
AllCCS[M+NH4]+134.332859911
AllCCS[M+Na]+135.632859911
AllCCS[M-H]-128.132859911
AllCCS[M+Na-2H]-128.932859911
AllCCS[M+HCOO]-129.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Indole-3-carboxaldehydeO=CC1=CNC2=C1C=CC=C22539.3Standard polar33892256
Indole-3-carboxaldehydeO=CC1=CNC2=C1C=CC=C21759.6Standard non polar33892256
Indole-3-carboxaldehydeO=CC1=CNC2=C1C=CC=C21839.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indole-3-carboxaldehyde,1TMS,isomer #1C[Si](C)(C)N1C=C(C=O)C2=CC=CC=C211904.0Semi standard non polar33892256
Indole-3-carboxaldehyde,1TMS,isomer #1C[Si](C)(C)N1C=C(C=O)C2=CC=CC=C211827.6Standard non polar33892256
Indole-3-carboxaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(C=O)C2=CC=CC=C212064.6Semi standard non polar33892256
Indole-3-carboxaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(C=O)C2=CC=CC=C211983.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde EI-B (Non-derivatized)splash10-00kp-7900000000-cfb69fae32949705791f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde EI-B (Non-derivatized)splash10-0007-2900000000-90cfb2317bcbb908e2e82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde EI-B (Non-derivatized)splash10-0007-2900000000-90cfb2317bcbb908e2e82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde EI-B (Non-derivatized)splash10-0007-2900000000-c43b940db5ef735c79d62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde GC-EI-TOF (Non-derivatized)splash10-00kk-2950000000-8901bc9a710fac996fbc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde GC-EI-TOF (Non-derivatized)splash10-00kb-2960000000-0b154d6ce8924292e9ed2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-252f37d7921252e01ac02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-868873ec5dc494bef7522017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde EI-B (Non-derivatized)splash10-00kp-7900000000-cfb69fae32949705791f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde EI-B (Non-derivatized)splash10-0007-2900000000-90cfb2317bcbb908e2e82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde EI-B (Non-derivatized)splash10-0007-2900000000-90cfb2317bcbb908e2e82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde EI-B (Non-derivatized)splash10-0007-2900000000-c43b940db5ef735c79d62018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde GC-EI-TOF (Non-derivatized)splash10-00kk-2950000000-8901bc9a710fac996fbc2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde GC-EI-TOF (Non-derivatized)splash10-00kb-2960000000-0b154d6ce8924292e9ed2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-252f37d7921252e01ac02018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Indole-3-carboxaldehyde GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-868873ec5dc494bef7522018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-carboxaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-0900000000-2f4c23a8137235ce4e952017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-carboxaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-carboxaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0007-2900000000-fcb37c6394c016a4e2d02015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde LC-ESI-QTOF , negative-QTOFsplash10-0006-0900000000-39d11dbd7bebe565fa942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde LC-ESI-QTOF , negative-QTOFsplash10-014l-0900000000-c9a64e9031a8d467a02b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde LC-ESI-QTOF , negative-QTOFsplash10-0006-0900000000-b7ccb1c640ee7aaf06b42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde LC-ESI-QTOF , negative-QTOFsplash10-014l-0900000000-d434c2e937c83d1ffd7c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde LC-ESI-QTOF , positive-QTOFsplash10-00kb-0900000000-597c804d77e9a7930c9e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde LC-ESI-QTOF , positive-QTOFsplash10-014i-2900000000-878ab4a0cfc6d8f0e9d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde LC-ESI-QTOF , positive-QTOFsplash10-00kf-9400000000-74dbc81ab5e6866559772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde LC-ESI-QTOF , positive-QTOFsplash10-00kf-9100000000-22b52274e9bec85c94882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde LC-ESI-QTOF , positive-QTOFsplash10-014i-3900000000-b8cbcf3139ea5a3136662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde LC-ESI-QTOF , positive-QTOFsplash10-014i-2900000000-94ec8ba0db56440ffc3f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde 35V, Positive-QTOFsplash10-00kf-9400000000-baa602f27188a3041af42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde 45V, Positive-QTOFsplash10-00kf-9100000000-345cf6df9ff740e5d9262021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde 25V, Positive-QTOFsplash10-014i-2900000000-878ab4a0cfc6d8f0e9d02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde 15V, Positive-QTOFsplash10-00kb-0900000000-597c804d77e9a7930c9e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde 35V, Positive-QTOFsplash10-0002-0900000000-3d2deb9c036b136fd16a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde 50V, Positive-QTOFsplash10-014i-1900000000-16d2415d939c5aaff4492021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde 30V, Negative-QTOFsplash10-014l-0900000000-d434c2e937c83d1ffd7c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde 30V, Negative-QTOFsplash10-014l-0900000000-c9a64e9031a8d467a02b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carboxaldehyde 35V, Negative-QTOFsplash10-00kf-0900000000-ba3a2cf1a036ce47cf692021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carboxaldehyde 10V, Positive-QTOFsplash10-0002-0900000000-68769392454e8a8bc1da2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carboxaldehyde 20V, Positive-QTOFsplash10-0002-0900000000-0be256e552c87fb9650a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carboxaldehyde 40V, Positive-QTOFsplash10-014i-2900000000-ae05266446e712d329cb2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carboxaldehyde 10V, Negative-QTOFsplash10-0006-0900000000-89f321c95d799e3073a82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carboxaldehyde 20V, Negative-QTOFsplash10-0006-0900000000-f63834b99989e7eab9cf2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carboxaldehyde 40V, Negative-QTOFsplash10-00kf-2900000000-7f76bc218a02b8adc1d02015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000934
KNApSAcK IDC00000112
Chemspider ID9838
KEGG Compound IDC08493
BioCyc IDINDOLE-3-CARBOXALDEHYDE
BiGG IDNot Available
Wikipedia LinkIndole-3-carboxaldehyde
METLIN IDNot Available
PubChem Compound10256
PDB IDI3A
ChEBI ID28238
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1251521
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roager HM, Licht TR: Microbial tryptophan catabolites in health and disease. Nat Commun. 2018 Aug 17;9(1):3294. doi: 10.1038/s41467-018-05470-4. [PubMed:30120222 ]
  2. Zhang LS, Davies SS: Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions. Genome Med. 2016 Apr 21;8(1):46. doi: 10.1186/s13073-016-0296-x. [PubMed:27102537 ]
  3. Kochen W, Buhner R, Otting W: [Identification of oxindole and 3-indolecarbaldehyde in the urine of patients with untreated phenylketonuria]. Hoppe Seylers Z Physiol Chem. 1972 Jul;353(7):1017-22. [PubMed:5073866 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transcription regulator activity
Specific function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular weight:
96146.7